Cocrystals of p-coumaric acid

Abstract

Disclosed herein are cocrystals of p-coumaric acid and nicotinamide. A 1:1 molar ratio and a 2:1 molar ratio of p-coumaric acid to nicotinamide are herein disclosed.

What is claimed is: 
     
       1. A cocrystal of p-coumaric acid and nicotinamide having a molar ratio of p-coumaric acid to nicotinamide of 2:1 having an x-ray powder diffraction pattern comprising one or more peaks at about 16.5°2θ, about 17.6°2θ, 19.0°2θ, 22.5°2θ, about 23.0°2θ, about 23.8°2θ, about 24.8°2θ, about 27.1°2θ, or about 27.3°2θ. 
     
     
       2. The cocrystal of  claim 1  having a DSC thermogram with an endotherm at about 174.1° C. 
     
     
       3. The cocrystal of  claim 1  having a  13 C solid-state NMR spectrum comprising one or more peaks at about 175.4 ppm, about 172.8 ppm, about 169.8 ppm, about 158.9 ppm, about 150.0 ppm, about 148.3 ppm, about 145.2 ppm, about 138.4 ppm, about 135.0 ppm, about 128.1 ppm, about 126.4 ppm, about 124.5 ppm, about 116.9 ppm, about 115.7 ppm, or about 110.5 ppm. 
     
     
       4. The cocrystal of  claim 2  having a  13 C solid-state NMR spectrum comprising a peak at about 158.9 ppm. 
     
     
       5. A pharmaceutical composition comprising at least one cocrystal of  claim 1  and at least one pharmaceutically acceptable carrier. 
     
     
       6. The cocrystal of  claim 2  having a  13 C solid state NMR spectrum comprising one or more peaks at about 175.4 ppm, about 172.8 ppm, about 169.8 ppm, about 158.9 ppm, about 150.0 ppm, about 148.3 ppm, about 145.2 ppm, about 138.4 ppm, about 135.0 ppm, about 128.1 ppm, about 126.4 ppm, about 124.5 ppm, about 116.9 ppm, about 115.7 ppm, or about 110.5 ppm.. 
     
     
       7. A cocrystal of p-coumaric acid and nicotinamide. 
     
     
       8. The cocrystal of  claim 7  having an x-ray powder diffraction pattern comprising one or more peaks at either (i) about 5.9°2θ, about 11.8°2θ, about 15.7°2θ, about 17.1°2θ, about 18.2°2θ, about 18.9°2θ, about 23.8°2θ, about 25.0°2θ, about 26.7°2θ, or about 28.4°2θ or (ii) about 16.5°2θ, about 17.6°2θ, about 19.0°2θ, about 22.5°2θ, about 23.0°2θ, about 23.8°2θ, about 24.8°2θ, about 27.1°2θ, or about 27.3°2θ. 
     
     
       9. The cocrystal of  claim 8 , wherein the molar ratio of p-cournaric acid to nicotinamide is 2:1. 
     
     
       10. The cocrystal of  claim 9  having a DSC thermogram with an endotherm at about 174° C. 
     
     
       11. The cocrystal of  claim 9  having a  13 C solid-state NMR spectrum comprising a peak at about 158.9 ppm.